


Seduce the Housekeeper

by littlefirefly31



Series: Kink/Request Fics [146]
Category: Supernatural
Genre: Bottom Sam, Crossdressing, M/M, maid kink
Language: English
Status: Completed
Published: 2015-08-10
Updated: 2015-08-10
Packaged: 2018-04-13 22:27:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 901
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4539807
Author URL: https://archiveofourown.org/users/littlefirefly31/pseuds/littlefirefly31
Summary: <blockquote class="userstuff">
              <p>Prompt: Can you do a maid!sam/Jared (doesn't matter which) and a top!Dean/Jensen please? If it's dean/sam then could dean have a maid kink and sam be embarrassed about being in a maid dress, please?</p>
            </blockquote>





	Seduce the Housekeeper

**Author's Note:**

> I'm on vacation (not from writing, i'm on a trip) so posting is hard but guess what i'm writing lots of prompts! which means i'll be posting! I have 10 prompts to fulfill and if it comes late it's not because i don't care its because i'm swamped!

**Prompt:** Can you do a maid! **sam** /Jared (doesn't matter which) and a top!Dean please? If it's dean/sam then could dean have a maid kink and sam be embarrassed about being in a maid dress, please?

 

“This is a terrible idea,” Sam grumbled.

Dean raked his eyes up Sam’s body. “I like it.”

Sam tried to smooth down the ruffles. “If someone walked in the motel right now they’d think you were trying to seduce the housekeeper.”

“I highly doubt any male housekeepers are dressed up like you.” Dean reached out and tugged on Sam’s black dress. “I spent good money on this outfit, I want you to do it justice.”

“What do you want me to say?” Sam asked. “You want me to say something like ‘you’ve been a dirty boy, I need to clean you up?’”

Dean smirked. “Well I certainly wouldn’t mind it. I would mind watching you ‘dust’ with your back to me and I can see that tight little dress ride up over your tight ass.”

Dean had purposely ordered the costume a size too small so it was tight on his curves and it made his legs look nice and long. “I’d even like it if you stood there and just let me drink you in. I can’t believe you did this for me.”

Sam blushed. “Yeah, neither can I.”

Dean walked over to Sam and slid his hand underneath the skirt. Sam blushed but his dick hardened as Dean’s hand crawled upwards. Dean cupped Sam’s plumping dick and grinned. “Next time I think we’ll put some panties on you. I’d love to feel some soft silk when I put my hand up your leg.”

Sam unconsciously spread his legs to allow Dean more space to work. “I want to shove this dress up just enough so I can see your hole, and then fuck you with the dress still on.”

Sam groaned. “Dean…”

“Not so embarrassed about the dress now, are you?” Dean purred. He flopped back down on the bed. “Entice me.”

“Entice y–,” Sam sighed. “Fine.” He brushed his hair back and walked towards Dean, swaying his hips. His muscular thighs were visible and Dean could see the base of Sam’s huge package. Sam’s nipples were perked and visible through the thin fabric. Dean wanted Sam underneath him _now_. Sam dropped onto his bed and crawled to Dean on his hands and knees. “I want you inside me.”

“Good plan,” Dean breathed. His hand fumbled on the nightstand to get the lube because he didn’t want to take his eyes off Sam and the way his hips still swayed on the bed. He uncapped it and drizzled some on his fingers. “Gonna open you up real good.”   
Sam shucked off his underwear and presented his ass to Dean. Dean rolled on top of Sam and shoved his finger in. Sam moaned and pushed his ass back down on Dean’s fingers. Dean added a second and fucked him on his fingers. “Your ass looks so hot in this costume, I swear to god.”

“Do you want to fuck me or talk?” Sam grumbled.

“Definitely fuck,” Dean replied. He shoved the hem of the dress up and shifted so the head of his cock was pushing against Sam’s hole. “Ready baby?”

“I was ready 10 minutes ago.”

“Smartass.” Dean shoved into his brother and moaned. “So tight, Sammy!”

“Fuck,” Sam groaned. “Come on, Dean, get on with it!”

“Brat.” Dean pulled out and then thrust into his brother again. Sam moaned and Dean tried to angle his thrusts to he could hit Sam’s prostate. He pulled out until the very tip of his cock remained and then shoved in to the hilt. Sam writhed underneath him and bunched his hands in the maid dress.

Dean’s eyes raked over the white apron and the soft white ruffles that tickled the back of Sam’s thighs. Sam humped the bed with his cock rubbing against the soft fabric of the dress. It was silky against his flesh and Sam moaned. His dick slipped against it but it wasn’t enough to bring him off. “Come on, Dean, touch me!”

Dean grunted as his hips pumped into his little brother. He was hitting Sam’s prostate on each push. “You will come on my dick alone.”

Sam loved the feeling of Dean’s dick twisting and turning and shoving inside his ass, but he didn’t know if it was enough. Even with the combined ecstasy of Dean stimulating his prostate Sam didn’t know if he could come. He rubbed off against the bed until his balls were tightening. “Fuck, Dean, I’m gonna come!”

“Yeah,” Dean moaned. His thrusts were stuttering and his breath came in short bursts. “Ah!” His orgasm exploded inside Sam and he collapsed on his back, fisting his fingers in the dress.

Sam gasped and bit the pillow when he felt himself start to come. “Fuck!” His balls spurted come against the bedspread.

Dean pulled his cock out and come drizzled down Sam’s thighs. He grabbed a tissue and cleaned them both up quickly, dabbing at the sweat on their faces. “So. Was it worth it?”

Sam pinched the fabric. “I guess.”

“Great.” Dean yawned. “I’m tired now. Shut up and let me sleep.”

Before Dean fell asleep, however, he made a mental note to check out any haunted hotels. Sam had an excellent cover outfit.


End file.
